US5079383A - Method of condensing n-phenyl carbamates - Google Patents
Method of condensing n-phenyl carbamates Download PDFInfo
- Publication number
- US5079383A US5079383A US07/556,993 US55699390A US5079383A US 5079383 A US5079383 A US 5079383A US 55699390 A US55699390 A US 55699390A US 5079383 A US5079383 A US 5079383A
- Authority
- US
- United States
- Prior art keywords
- phenylcarbamate
- group
- isomers
- methyl
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- -1 zinc halide Chemical class 0.000 claims abstract description 14
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 10
- 239000011701 zinc Substances 0.000 claims abstract description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 18
- IAGUPODHENSJEZ-UHFFFAOYSA-N methyl n-phenylcarbamate Chemical compound COC(=O)NC1=CC=CC=C1 IAGUPODHENSJEZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011592 zinc chloride Substances 0.000 claims description 9
- UVMTZTPUIFOAGM-UHFFFAOYSA-N (3-chlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC(Cl)=C1 UVMTZTPUIFOAGM-UHFFFAOYSA-N 0.000 claims description 8
- VTONZKDPQTYHLV-UHFFFAOYSA-N (3-methylphenyl) carbamate Chemical compound CC1=CC=CC(OC(N)=O)=C1 VTONZKDPQTYHLV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 235000005074 zinc chloride Nutrition 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 5
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 4
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229920002866 paraformaldehyde Polymers 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
- QDZXCXBFZLLQFT-UHFFFAOYSA-N propyl n-phenylcarbamate Chemical compound CCCOC(=O)NC1=CC=CC=C1 QDZXCXBFZLLQFT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- UYVWNPAMKCDKRB-UHFFFAOYSA-N 1,2,4,5-tetraoxane Chemical compound C1OOCOO1 UYVWNPAMKCDKRB-UHFFFAOYSA-N 0.000 claims description 2
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims description 2
- ULLHJKVIRXQCJN-UHFFFAOYSA-N 2-methylpropyl n-phenylcarbamate Chemical compound CC(C)COC(=O)NC1=CC=CC=C1 ULLHJKVIRXQCJN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- ZTIMKJROOYMUMU-UHFFFAOYSA-N butyl n-phenylcarbamate Chemical compound CCCCOC(=O)NC1=CC=CC=C1 ZTIMKJROOYMUMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- CEUNIYVZFAQQSI-UHFFFAOYSA-N cyclohexyl n-phenylcarbamate Chemical compound C1CCCCC1OC(=O)NC1=CC=CC=C1 CEUNIYVZFAQQSI-UHFFFAOYSA-N 0.000 claims description 2
- HNEGSWZZYCZACE-UHFFFAOYSA-N hexyl n-phenylcarbamate Chemical compound CCCCCCOC(=O)NC1=CC=CC=C1 HNEGSWZZYCZACE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BIYXGLPPMRDUNY-UHFFFAOYSA-N pentyl n-phenylcarbamate Chemical compound CCCCCOC(=O)NC1=CC=CC=C1 BIYXGLPPMRDUNY-UHFFFAOYSA-N 0.000 claims description 2
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 2
- KZZHPWMVEVZEFG-UHFFFAOYSA-N tert-butyl n-phenylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1 KZZHPWMVEVZEFG-UHFFFAOYSA-N 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000012022 methylating agents Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 19
- 238000009833 condensation Methods 0.000 abstract description 4
- 230000005494 condensation Effects 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 12
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 11
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 10
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- CNFSVGBXMCZHQF-UHFFFAOYSA-N methyl n-[(n-methoxycarbonylanilino)methyl]-n-phenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OC)CN(C(=O)OC)C1=CC=CC=C1 CNFSVGBXMCZHQF-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HOMDJHGZAAKUQV-UHFFFAOYSA-N 1-(propoxymethoxy)propane Chemical compound CCCOCOCCC HOMDJHGZAAKUQV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- BPGDAMSIGCZZLK-UHFFFAOYSA-N acetyloxymethyl acetate Chemical compound CC(=O)OCOC(C)=O BPGDAMSIGCZZLK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- OTSJRHVZRARHBC-UHFFFAOYSA-N benzylbenzene;carbamic acid Chemical class NC(O)=O.NC(O)=O.C=1C=CC=CC=1CC1=CC=CC=C1 OTSJRHVZRARHBC-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- BBOLNFYSRZVALD-UHFFFAOYSA-N 1,2-diiodobenzene Chemical compound IC1=CC=CC=C1I BBOLNFYSRZVALD-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- QBELEDRHMPMKHP-UHFFFAOYSA-N 1-bromo-2-chlorobenzene Chemical compound ClC1=CC=CC=C1Br QBELEDRHMPMKHP-UHFFFAOYSA-N 0.000 description 1
- NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- PQSWCVYWEGIBPY-UHFFFAOYSA-N 2,2-dinitroethylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)CC1=CC=CC=C1 PQSWCVYWEGIBPY-UHFFFAOYSA-N 0.000 description 1
- DYSXLQBUUOPLBB-UHFFFAOYSA-N 2,3-dinitrotoluene Chemical compound CC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O DYSXLQBUUOPLBB-UHFFFAOYSA-N 0.000 description 1
- XAWCLWKTUKMCMO-UHFFFAOYSA-N 2-nitroethylbenzene Chemical compound [O-][N+](=O)CCC1=CC=CC=C1 XAWCLWKTUKMCMO-UHFFFAOYSA-N 0.000 description 1
- GHLOZOFSZVNFMD-UHFFFAOYSA-N 3,3-dinitropropylbenzene Chemical compound [O-][N+](=O)C([N+]([O-])=O)CCC1=CC=CC=C1 GHLOZOFSZVNFMD-UHFFFAOYSA-N 0.000 description 1
- ZROLMSLMPMSLRM-UHFFFAOYSA-N 3-nitropropylbenzene Chemical compound [O-][N+](=O)CCCC1=CC=CC=C1 ZROLMSLMPMSLRM-UHFFFAOYSA-N 0.000 description 1
- QTOUMDHSKLLTAL-UHFFFAOYSA-N 5,5-dinitropentylbenzene Chemical compound [N+](=O)([O-])C(CCCCC1=CC=CC=C1)[N+](=O)[O-] QTOUMDHSKLLTAL-UHFFFAOYSA-N 0.000 description 1
- ZWBVUKQTAIOBJG-UHFFFAOYSA-N 5-nitropentylbenzene Chemical compound [O-][N+](=O)CCCCCC1=CC=CC=C1 ZWBVUKQTAIOBJG-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 229920006311 Urethane elastomer Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-BJUDXGSMSA-N nitromethane Chemical group [11CH3][N+]([O-])=O LYGJENNIWJXYER-BJUDXGSMSA-N 0.000 description 1
- VLZLOWPYUQHHCG-UHFFFAOYSA-N nitromethylbenzene Chemical compound [O-][N+](=O)CC1=CC=CC=C1 VLZLOWPYUQHHCG-UHFFFAOYSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
Abstract
Description
TABLE 1 ______________________________________ E4 E5 ______________________________________ Conversion of N-phenylcarbamate 104 74 (%) Selectivity 4,4'-diphenylmethanedicarbamate 71 96 2,4'-diphenylmethanedicarbamate 3.1 4.6 intermediate* 0.0 0.0 polynuclear compound** 0.4 3.5 Yield 4,4'-diphenylmethanedicarbamate 74 71 2,4'-diphenylmethanedicarbamate 3.2 3.4 ______________________________________ *Example 4: bis(Ncarbomethoxyanilino)methane and methyl(Ncarbomethoxyanilinomethyl)phenylcarbamate which are intermediates having a methyleneamino bond Example 5: bis(Ncarboethoxyanilino)methane and ethyl(Ncarboethoxyanilinomethyl)phenylcarbamate which are intermediates having a methyleneamino bond **tri and more nuclear polymethylenepolyphenyl carbamates
Claims (8)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1-195328 | 1989-07-27 | ||
JP1195328A JPH0358965A (en) | 1989-07-27 | 1989-07-27 | Condensation of n-phenylcarbamtes |
Publications (1)
Publication Number | Publication Date |
---|---|
US5079383A true US5079383A (en) | 1992-01-07 |
Family
ID=16339340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/556,993 Expired - Fee Related US5079383A (en) | 1989-07-27 | 1990-07-25 | Method of condensing n-phenyl carbamates |
Country Status (9)
Country | Link |
---|---|
US (1) | US5079383A (en) |
EP (1) | EP0410684B1 (en) |
JP (1) | JPH0358965A (en) |
KR (1) | KR0179659B1 (en) |
CN (1) | CN1028522C (en) |
AT (1) | ATE114641T1 (en) |
CA (1) | CA2022052A1 (en) |
DE (1) | DE69014464T2 (en) |
DK (1) | DK0410684T3 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5302634A (en) * | 1992-10-15 | 1994-04-12 | Hoppmann Corporation | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5369147A (en) * | 1992-10-15 | 1994-11-29 | Ecomat, Inc. | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5508315A (en) * | 1992-10-15 | 1996-04-16 | Ecomat, Inc. | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5604266A (en) * | 1992-10-15 | 1997-02-18 | Ecomat, Inc. | Cured unsaturated polyest-polyurethane highly filled resin materials and process for preparing them |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63212605A (en) * | 1987-03-02 | 1988-09-05 | Daifuku Co Ltd | Article taking-out equipment |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2946768A (en) * | 1957-08-12 | 1960-07-26 | Bayer Ag | Condensation products of carbamic acid esters |
US4699994A (en) * | 1985-09-18 | 1987-10-13 | Nippon Kokan Kabushiki Kaisha | Method of manufacturing diphenylmethane dicarbamic acid diesters |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4202986A (en) * | 1979-02-12 | 1980-05-13 | Atlantic Richfield Company | Preparation of diphenylmethane dicarbamates and polymethylene polyphenyl carbamates with Lewis acid catalysts intercalated in graphite |
DE3202687A1 (en) * | 1982-01-28 | 1983-08-04 | Basf Ag, 6700 Ludwigshafen | Process for the preparation of methylenebisphenylcarbamic esters and polymethylenepolyphenylcarbamic esters |
-
1989
- 1989-07-27 JP JP1195328A patent/JPH0358965A/en active Pending
-
1990
- 1990-07-24 AT AT90308075T patent/ATE114641T1/en not_active IP Right Cessation
- 1990-07-24 DE DE69014464T patent/DE69014464T2/en not_active Expired - Fee Related
- 1990-07-24 DK DK90308075.2T patent/DK0410684T3/en active
- 1990-07-24 EP EP90308075A patent/EP0410684B1/en not_active Expired - Lifetime
- 1990-07-25 US US07/556,993 patent/US5079383A/en not_active Expired - Fee Related
- 1990-07-26 KR KR1019900011384A patent/KR0179659B1/en not_active IP Right Cessation
- 1990-07-26 CA CA002022052A patent/CA2022052A1/en not_active Abandoned
- 1990-07-27 CN CN90107070A patent/CN1028522C/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2946768A (en) * | 1957-08-12 | 1960-07-26 | Bayer Ag | Condensation products of carbamic acid esters |
US4699994A (en) * | 1985-09-18 | 1987-10-13 | Nippon Kokan Kabushiki Kaisha | Method of manufacturing diphenylmethane dicarbamic acid diesters |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5302634A (en) * | 1992-10-15 | 1994-04-12 | Hoppmann Corporation | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5369147A (en) * | 1992-10-15 | 1994-11-29 | Ecomat, Inc. | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5508315A (en) * | 1992-10-15 | 1996-04-16 | Ecomat, Inc. | Cured unsaturated polyester-polyurethane hybrid highly filled resin foams |
US5604266A (en) * | 1992-10-15 | 1997-02-18 | Ecomat, Inc. | Cured unsaturated polyest-polyurethane highly filled resin materials and process for preparing them |
Also Published As
Publication number | Publication date |
---|---|
CN1028522C (en) | 1995-05-24 |
EP0410684A2 (en) | 1991-01-30 |
JPH0358965A (en) | 1991-03-14 |
EP0410684B1 (en) | 1994-11-30 |
DE69014464T2 (en) | 1995-05-11 |
DK0410684T3 (en) | 1995-01-16 |
CA2022052A1 (en) | 1991-01-28 |
CN1050378A (en) | 1991-04-03 |
EP0410684A3 (en) | 1992-03-11 |
DE69014464D1 (en) | 1995-01-12 |
KR0179659B1 (en) | 1999-05-15 |
ATE114641T1 (en) | 1994-12-15 |
KR910002783A (en) | 1991-02-26 |
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